Light-Induced, Iron-Promoted Formation of Benzotetraphenones via Paternò–Büchi Photorearrangement/Electrocyclization: A Route to Polyaromatic Scaffolds

Ícaro A. O. Bozzi; Dandara S. Borges; Bruno Dival; Willian X. C. Oliveira; Luana A. Machado; Renata G. Almeida; Maria H. Araujo; Edmond Gravel; Eufrânio N. da Silva Júnior; Guilherme A. M. Jardim

doi:10.1055/a-2705-9158

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2705-9158

Letter

Published as part of the Special Topic Alkynes in Organic Synthesis

Light-Induced, Iron-Promoted Formation of Benzotetraphenones via Paternò–Büchi Photorearrangement/Electrocyclization: A Route to Polyaromatic Scaffolds

Authors

Ícaro A. O. Bozzi

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Dandara S. Borges

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Bruno Dival

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Willian X. C. Oliveira

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Luana A. Machado

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Renata G. Almeida

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Maria H. Araujo

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Edmond Gravel

²DRF/Joliot/DMTS/SCBM, CEA, Gif-sur-Yvette, France
Eufrânio N. da Silva Júnior

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Guilherme A. M. Jardim

¹Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

Abstract

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Abstract

We report a light-induced, iron-promoted method for the synthesis of polyaromatic benzotetraphenone derivatives via a tandem [2+2] Paternò–Büchi photorearrangement/electrocyclization pathway. Irradiation of anthraquinone with diphenylacetylenes under 370 nm LED light in the presence of FeCl₃ afforded novel polyaromatic scaffolds in excellent yields. The structures of the products were confirmed by single-crystal X-ray diffraction, revealing planar, rigid frameworks with promising photophysical properties. This strategy offers a new platform for constructing highly conjugated, luminescent molecules from simple precursors under mild conditions.

Keywords

Photochemistry - Photorearrangement - Paternò–Büchi - Lewis acid catalysis - Benzotetraphenones

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